Anne McKee Artists Fund Fine Arts Auction

Oil painting by Joanne Sloan depicting a tranquil seascape in soft blues, purples, and aquamarine tones. Billowing clouds fill the sky above calm turquoise water, with a faint silhouette of a distant lighthouse on the horizon. Created for the Anne McKee Art Auction.

Friday, February 27, 5pm (doors open 4:15)

Helmerich Theater

sponsored by the Anne and G. Ross McKee, Jr. Charitable Fund

image: Joanne Sloan

Now in its 31st year, the Anne McKee Fine Art Auction returns to The Studios with an evening celebrating the creativity of the Keys. Guests can preview and purchase artwork throughout February, then join us on auction night for gourmet hors d’oeuvres, champagne, and live music by Bobby Nesbitt before the bidding begins.

Each participating artist receives 50% of the sale of their work, with the remaining proceeds funding grants for local visual, performing, and literary artists through the Anne McKee Artists Fund.

Ricky Skaggs and Sharon White

Old Town New Folk

Concert series sponsored by Blue Heaven (click here to view the full lineup →)
Ricky Skaggs and Sharon White smile warmly outdoors, each holding their instruments — Skaggs with his mandolin, White with her guitar. Sunlight filters through the trees behind them, capturing the warmth, harmony, and enduring partnership that define their decades-long musical and personal journey.

Tuesday, March 24, 7pm

Helmerich Theater

$125 front row, $85 general admission

Wednesday, March 25, 7pm

Hugh’s View

$125 front row, $95 general admission

This season of Old Town New Folk closes with an evening of bluegrass brilliance and pure harmony, as two of country music’s most celebrated voices share the stage.

Ricky Skaggs and Sharon White are a musical partnership woven from love, legacy, and more than six decades of song. Earning 12 #1 hit singles, 15 GRAMMY® Awards, 13 IBMA Awards, nine ACM Awards, eight CMA Awards (including Entertainer of the Year), along with inductions into the Bluegrass Music and Country Music Hall of Fame, Ricky Skaggs is truly a pioneer of Bluegrass and Country music. Since his beginnings in music over 60 years ago, the Grand Ole Opry member has released more than 30 albums and performed thousands of live shows with his ace backing band, Kentucky Thunder. He started his own record label, Skaggs Family Records, in 1997, releasing 12 consecutive GRAMMY®-nominated albums and has published his autobiography, “Kentucky Traveler.”

Sharon White is a member of beloved Country-Gospel family band, The Whites, and has been making music alongside her father Buck and sister Cheryl for more than five decades. They originally began as a Bluegrass group, but the family trio became well known for their string of Country hits in the 1980s, including “Hangin’ Around,” “Give Me Back That Old Familiar Feeling,” and “Pins and Needles.” The Whites are Grand Ole Opry members and were involved in the 2001 hit movie and soundtrack, O Brother, Where Art Thou? They have gone on to win GRAMMY®, CMA and Dove Awards, among others.

Together, Skaggs and White create music rooted in faith, family, and the enduring joy of tradition. Their performances shimmer with intimacy and grace — a heartfelt finale to this season’s Old Town New Folk series.

Old Town New Folk is underwritten by Nick and Lorie Howley, with additional support from Doug and Sherri Montgomery, John and Marilyn Rintamaki, Nell Smets, and Michael Blades and Kathy Kilroy. 

Jake Shimabukuro

Old Town New Folk

Concert series sponsored by Blue Heaven (click here to view the full lineup →)
Ukulele virtuoso Jake Shimabukuro stands against a vivid red wall, strumming his instrument with a relaxed smile. Dressed in a black leather jacket and dark shirt, he radiates calm confidence and creative energy, embodying the boundary-breaking spirit that has made him one of the world’s most celebrated ukulele players.

Tuesday, March 10, 7pm

Helmerich Theater

$125 front row, $85 general admission

Wednesday, March 11, 7pm

Hugh’s View

$125 front row, $95 general admission

Hailed as the “Jimi Hendrix of the ukulele,” Jake Shimabukuro has taken the four-string instrument to breathtaking new heights. Since first gaining worldwide fame with his viral rendition of George Harrison’s “While My Guitar Gently Weeps,” Shimabukuro has toured the globe—from the Hollywood Bowl to the Sydney Opera House—mesmerizing audiences with his lightning-fast technique and genre-defying sound.

Over the course of more than a dozen albums, the Hawaii-born musician has collaborated with an astonishing roster that includes Yo-Yo Ma, Jimmy Buffett, Bela Fleck, Bette Midler, and Willie Nelson. His most recent project, Blues Experience, finds him joining forces with Fleetwood Mac co-founder Mick Fleetwood for an exhilarating take on blues classics, reimagined through ukulele and percussion.

A passionate collaborator and storyteller, Shimabukuro channels joy, innovation, and pure musical spirit in every note. His concerts are dazzling celebrations of connection—proof that even the smallest instrument can carry the biggest sound.

Old Town New Folk is underwritten by Nick and Lorie Howley, with additional support from Doug and Sherri Montgomery, John and Marilyn Rintamaki, Nell Smets, and Michael Blades and Kathy Kilroy. 

Jon Langford

Old Town New Folk

Concert series sponsored by Blue Heaven (click here to view the full lineup →)
Musician and artist Jon Langford stands before a brick wall decorated with his own artwork, holding an acoustic guitar mid-strum. His serious expression contrasts with the vivid, folk-inspired imagery behind him, capturing the creative fusion of punk energy and Americana roots that defines his work.

Tuesday, March 3, 7pm

Helmerich Theater

$100 front row, $50 general admission

Wednesday, March 4, 7pm

Hugh’s View

$125 front row, $70 general admission

Welsh-born and Chicago-based Jon Langford is a musical shapeshifter—punk pioneer, country crooner, painter, radio host, and storyteller. A founding member of the legendary punk band The Mekons, Langford helped redefine what folk and country could be when filtered through the raw edge of rock and rebellion. His later projects, including The Three Johns and The Pine Valley Cosmonauts, reflect his lifelong curiosity and collaborative spirit, bringing together musicians across genres and generations.

A true renaissance man, Langford is also a prolific visual artist whose striking portraits of country icons such as Hank Williams and Johnny Cash have become emblematic of his deep affection for American roots music. Whether on stage or on canvas, his work hums with humor, humanity, and a restless creative energy that’s distinctly his own.

Old Town New Folk is underwritten by Nick and Lorie Howley, with additional support from Doug and Sherri Montgomery, John and Marilyn Rintamaki, Nell Smets, and Michael Blades and Kathy Kilroy. 

Rachael Sage

Old Town New Folk

Concert series sponsored by Blue Heaven (click here to view the full lineup →)
Singer-songwriter Rachael Sage poses against a colorful, abstract backdrop. She wears bright, patterned clothing, turquoise earrings, and flowers in her hair, radiating creativity and joyful energy.

Tuesday, February 17, 7pm

Helmerich Theater

$100 front row, $50 general admission

Wednesday, February 18, 6pm

Hugh’s View

$125 front row, $70 general admission

A vibrant force in folk-pop, Rachael Sage has spent her career defying categories and expectations. Since founding her own label, MPress Records, the New York-based artist has released a steady stream of colorful, heartfelt albums that blend poetic lyricism with infectious melodies. She has toured alongside icons such as Rufus Wainwright, Ani DiFranco, Shawn Colvin, and Judy Collins, and her live shows are known for their humor, vulnerability, and bold theatrical flair.

A six-time Independent Music Award winner and John Lennon Songwriting Contest Grand Prize recipient, Sage is also a visual artist and former ballet dancer who once performed with the New York City Ballet. Beyond the stage, she is a “cancer thriver” and passionate advocate, using her music to raise awareness and funds for causes from women’s health to youth homelessness. With her signature blend of resilience and radiance, Sage transforms every performance into an inspiring celebration of art and survival.

Old Town New Folk is underwritten by Nick and Lorie Howley, with additional support from Doug and Sherri Montgomery, John and Marilyn Rintamaki, Nell Smets, and Michael Blades and Kathy Kilroy. 

John McCutcheon

Old Town New Folk

Concert series sponsored by Blue Heaven (click here to view the full lineup →)
Folk musician John McCutcheon smiles warmly while holding a banjo across his chest. He wears a striped shirt and dark vest, standing before a wooden backdrop that evokes the roots and warmth of traditional folk music.

Tuesday, February 3, 7pm

Helmerich Theater

$75 front row, $50 general admission

Wednesday, February 4, 6pm

Hugh’s View

$100 front row, $70 general admission

For nearly five decades, John McCutcheon has been a cornerstone of American folk music, earning the title of “folk music’s Rustic Renaissance Man” (Washington Post). A gifted multi-instrumentalist—master of guitar, fiddle, banjo, and especially the rare hammer dulcimer—McCutcheon is also a prolific songwriter, storyteller, and activist with more than 30 recordings and seven Grammy nominations to his name.

McCutcheon’s music is deeply rooted in tradition, shaped by his early apprenticeships with Appalachian masters in Kentucky coal camps, union halls, and country churches. From those beginnings, he developed a voice that bridges generations, blending traditional ballads, original songs, and rich storytelling. His artistry has earned praise from peers and icons alike: Pete Seeger called him “one of the best musicians in the USA,” while Johnny Cash hailed him as “the most impressive instrumentalist I’ve ever heard.”

Equally at home on festival stages, symphony halls, and school auditoriums, McCutcheon has built a career on connection—bringing audiences of all ages into the shared joy of music. His live performances are renowned for their warmth, humor, and vitality, leaving listeners with the sense they’ve spent an evening with an old friend.

Old Town New Folk is underwritten by Nick and Lorie Howley, with additional support from Doug and Sherri Montgomery, John and Marilyn Rintamaki, Nell Smets, and Michael Blades and Kathy Kilroy. 

Susan Werner

Old Town New Folk

Concert series sponsored by Blue Heaven (click here to view the full lineup →)
Musician Susan Werner performs on stage, smiling as she sings into a microphone while playing a grand piano under warm stage lights.

Tuesday, January 20, 7pm

Helmerich Theater

$85 front row, $50, $40 mbrs.

Wednesday, January 21, 6pm

Hugh’s View

$100 front row, $70, $60 mbrs.

Over the course of her twenty five year career, Susan Werner has earned a reputation as “one of the most innovative songwriters working today” (Chicago Tribune). With formidable chops on guitar (she began playing at age 5) and piano (she was a guest on Marian McPartland’s Piano Jazz), along with a graduate degree in voice performance, her shows are a one-woman master class in musicianship. Although best known as an acoustic songwriter that came up through coffeehouses and folk festivals, the Chicago-based artist has written songs in the style of Gershwin and Cole Porter (I Can’t Be New, 2004), gospel music (The Gospel Truth, 2007), traditional Cuban “son” (An American In Havana, 2016), and New Orleans junk piano (NOLA, 2019). In 2014 she composed the music and lyrics to the musical theater score Bull Durham, The Musical (MGM). Her songs have been recorded by Tom Jones, Michael Feinstein, and Shemekia Copeland, and her latest recording of originals, The Birds of Florida, took flight in 2022.

Old Town New Folk is underwritten by Nick and Lorie Howley, with additional support from Doug and Sherri Montgomery, John and Marilyn Rintamaki, Nell Smets, and Michael Blades and Kathy Kilroy. 

Holiday Makers Market

Shop, Sculpt & Sip: browse artisan goods, paint your own ornament, and toast the season!

A collection of holiday gift bags in red and brown, filled with tissue paper and decorated with festive tags and snowflake ornaments.

Saturday, November 29, 10am-3pm

Vendors will be featured throughout the building + Hugh’s View!

Free and open to the public

Celebrate Small Business Saturday in true Key West style at The Studios’ annual Holiday Makers Market! Wander through every floor of our building and discover treasures from local artists and artisans—perfect for everyone on your list (and maybe a little something for yourself, too).

Step into the Helmerich Theater, transformed into a magical snowglobe with Christmas music and twinkling projections, or browse the Sanger Gallery, airy and bright with plenty of street-front energy. Don’t miss our newest addition: Hugh’s View, where you can sip holiday cocktails from the bar, enjoy open-air shopping, and maybe even catch a little live music.

On the third floor, you’ll find an open classroom set up for DIY ornament painting—drop in, use our supplies, and make your own festive keepsake with paint, glitter, or whatever sparks your imagination. Plus our studio artists may open their studios to share and sell their work, offering a glimpse into their creative spaces.

With the whole building brimming with creativity, festive vibes, and handmade gifts, you’ll want to plan to linger. And while you’re here, stop by our Museum Store for unique, exclusive and handmade goods from The Studios.

Anfinson: Portrait of an artist

work-in-progress preview screening

A Documentary Film by Cassidy Rast & Odin Wadleigh

Promotional still for the documentary “Anfinson: Portrait of an Artist,” showing a close-up of a window reflecting tree branches, with a cluster of paintbrushes visible through the glass. White text reads: “ANFINSON Portrait of an Artist — A film by Cassidy Rast and Odin Wadleigh.”

Join us for a work-in-progress preview screening of Anfinson: Portrait of an Artist. The documentary film offers an intimate and cinematic glimpse into the journey of one of Key West’s most celebrated painters. Directed by award-winning filmmakers Cassidy Rast and Odin Wadleigh, the documentary traces Anfinson’s formative years and young adulthood, the pivotal experiences that shaped his creative voice, and his present-day life as an artist.

The film captures not only the physical challenges he faces, but also the profound ways the island community fuels his inspiration and resilience. More than a portrait, it is a meditation on art, perseverance, and belonging.

Both special evenings include a live interactive performance by Kyla Piscopink to open the evening and a post-screening Q&A with the filmmakers, plus a rooftop reception on Hugh’s View after the show!

Southernmost Youth Orchestra Concert

Sunday, November 9, 5pm

Helmerich Theater

Free and open to the public

Experience the magic of the Southernmost Youth Orchestra! Join us for an inspiring performance by a talented group of young local string musicians. Under the direction of Irie Monte, these passionate performers bring energy, heart, and vibrant sound to every note. From classical favorites to contemporary selections, this concert showcases the rising stars of our southernmost community.